CHEBI:27386 - cinnamic acid

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ChEBI Name cinnamic acid
ChEBI ID CHEBI:27386
Definition A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:23250, CHEBI:3710
Supplier Information ZINC000263614187
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Formula C9H8O2
Net Charge 0
Average Mass 148.15862
Monoisotopic Mass 148.05243
InChI InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)
InChIKey WBYWAXJHAXSJNI-UHFFFAOYSA-N
SMILES [H]C(=Cc1ccccc1)C(O)=O
Metabolite of Species Details
Cinnamomum aromaticum (NCBI:txid119260) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cinnamic acid (CHEBI:27386) has role plant metabolite (CHEBI:76924)
cinnamic acid (CHEBI:27386) is a cinnamic acids (CHEBI:23252)
cinnamic acid (CHEBI:27386) is a styrenes (CHEBI:26799)
cinnamic acid (CHEBI:27386) is conjugate acid of cinnamate (CHEBI:23248)
Incoming (3E)-4-[3-(2-hydroxyethyl)-1H-indol-5-yl]but-3-en-2-one (CHEBI:210830) has functional parent cinnamic acid (CHEBI:27386)
(E)-1-Cinnamoylpyrrolidine (CHEBI:187055) has functional parent cinnamic acid (CHEBI:27386)
(E)-Herclavine (CHEBI:174123) has functional parent cinnamic acid (CHEBI:27386)
(E)-N-Cinnamoylpiperidine (CHEBI:157738) has functional parent cinnamic acid (CHEBI:27386)
1-(1-benzimidazolyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one (CHEBI:92061) has functional parent cinnamic acid (CHEBI:27386)
1-(2,4-dichlorophenyl)-5-(dimethylamino)-3-penta-1,4-dienone (CHEBI:115743) has functional parent cinnamic acid (CHEBI:27386)
1-(3,4-dihydro-1H-isoquinolin-2-yl)-3-(4-methylphenyl)-2-propen-1-one (CHEBI:105723) has functional parent cinnamic acid (CHEBI:27386)
1-(3-furanyl)-3-(4-methoxyphenyl)-2-propen-1-one (CHEBI:108249) has functional parent cinnamic acid (CHEBI:27386)
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]piperidin-2-one (CHEBI:182908) has functional parent cinnamic acid (CHEBI:27386)
1-[1-oxo-3-(3,4,5-trimethoxyphenyl)prop-2-enyl]-2,3-dihydropyridin-6-one (CHEBI:92424) has functional parent cinnamic acid (CHEBI:27386)
1-[4-(3,4-dihydroxyphenyl)-6-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]ethanone (CHEBI:112169) has functional parent cinnamic acid (CHEBI:27386)
1-Cinnamoylpyrrolidine (CHEBI:157709) has functional parent cinnamic acid (CHEBI:27386)
2,3-dihydroxycinnamic acid (CHEBI:48681) has functional parent cinnamic acid (CHEBI:27386)
2-(1H-benzimidazol-2-yl)-3-(3-chloro-5-ethoxy-4-methoxyphenyl)-1-(4-morpholinyl)-2-propen-1-one (CHEBI:108116) has functional parent cinnamic acid (CHEBI:27386)
3-(1,3-benzodioxol-5-yl)-1-(5-methyl-2-furanyl)-2-propen-1-one (CHEBI:116178) has functional parent cinnamic acid (CHEBI:27386)
3-(2,5-dimethoxyphenyl)-N-methyl-N-[2-(4-methylanilino)-2-oxoethyl]-2-propenamide (CHEBI:117129) has functional parent cinnamic acid (CHEBI:27386)
3-(2-chlorophenyl)-1-(1H-pyrrol-2-yl)-2-propen-1-one (CHEBI:115516) has functional parent cinnamic acid (CHEBI:27386)
3-(2-chlorophenyl)-N-[[[(5-methyl-1H-pyrazol-3-yl)-oxomethyl]hydrazo]-sulfanylidenemethyl]-2-propenamide (CHEBI:113185) has functional parent cinnamic acid (CHEBI:27386)
3-(3,4-dichlorophenyl)-N-(4,5-dihydrothiazol-2-yl)-2-propenamide (CHEBI:95276) has functional parent cinnamic acid (CHEBI:27386)
3-(3,4-dimethoxyphenyl)-N-[[(1-oxo-2-thiophen-2-ylethyl)hydrazo]-sulfanylidenemethyl]-2-propenamide (CHEBI:120058) has functional parent cinnamic acid (CHEBI:27386)
3-(3-bromo-4-methoxyphenyl)-N,N-di(propan-2-yl)-2-propenamide (CHEBI:123153) has functional parent cinnamic acid (CHEBI:27386)
3-(4-bromophenyl)-1-(2-methyl-5,6,7,8-tetrahydroquinolin-3-yl)-2-propen-1-one (CHEBI:115658) has functional parent cinnamic acid (CHEBI:27386)
3-(4-fluorophenyl)-N-[[[oxo(2-pyrazinyl)methyl]hydrazo]-sulfanylidenemethyl]-2-propenamide (CHEBI:107259) has functional parent cinnamic acid (CHEBI:27386)
3-(4-methoxyphenyl)-N-[[[oxo(thiophen-2-yl)methyl]hydrazo]-sulfanylidenemethyl]-2-propenamide (CHEBI:109605) has functional parent cinnamic acid (CHEBI:27386)
3-(4-tert-butylphenyl)-N-(4,5-dihydrothiazol-2-yl)-2-propenamide (CHEBI:112368) has functional parent cinnamic acid (CHEBI:27386)
3-[1-[(2,4-dichlorophenyl)methyl]-5-fluoro-3-methyl-7-indolyl]-N-[(4,5-dichloro-2-thiophenyl)sulfonyl]-2-propenamide (CHEBI:95012) has functional parent cinnamic acid (CHEBI:27386)
4,6-dimethyl-3-[1-oxo-3-(4-propan-2-ylphenyl)prop-2-enyl]-1H-pyridin-2-one (CHEBI:116930) has functional parent cinnamic acid (CHEBI:27386)
4,6-dimethyl-3-[3-(1-naphthalenyl)-1-oxoprop-2-enyl]-1H-pyridin-2-one (CHEBI:120966) has functional parent cinnamic acid (CHEBI:27386)
4-(1-naphthalenyl)-2-oxo-3-(2-quinolinyl)-3-butenoic acid (CHEBI:122033) has functional parent cinnamic acid (CHEBI:27386)
4-(3-chlorophenyl)-2-oxo-3-(2-quinolinyl)-3-butenoic acid (CHEBI:108030) has functional parent cinnamic acid (CHEBI:27386)
4-(3-Hydroxy-2-naphthyl)-2-oxobut-3-enoic acid (CHEBI:80381) has functional parent cinnamic acid (CHEBI:27386)
4-methoxycinnamic acid (CHEBI:48541) has functional parent cinnamic acid (CHEBI:27386)
4-oxo-3-(phenylmethylene)pentanoic acid (CHEBI:109554) has functional parent cinnamic acid (CHEBI:27386)
5-[3-(2-chlorophenyl)-1-oxoprop-2-enyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester (CHEBI:113036) has functional parent cinnamic acid (CHEBI:27386)
5-[3-(2-fluorophenyl)-1-oxoprop-2-enyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester (CHEBI:109377) has functional parent cinnamic acid (CHEBI:27386)
5-[3-(3-chlorophenyl)-1-oxoprop-2-enyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester (CHEBI:108020) has functional parent cinnamic acid (CHEBI:27386)
6,6,6-trifluoro-5-hydroxy-1,5-diphenyl-1-hexen-3-one (CHEBI:113014) has functional parent cinnamic acid (CHEBI:27386)
acetic acid [2-[2-(1-oxo-3-phenylprop-2-enyl)-3-phenyl-3,4-dihydropyrazol-5-yl]phenyl] ester (CHEBI:105087) has functional parent cinnamic acid (CHEBI:27386)
alkyl cinnamate (CHEBI:17958) has functional parent cinnamic acid (CHEBI:27386)
cadiolide B (CHEBI:188604) has functional parent cinnamic acid (CHEBI:27386)
cinepazide (CHEBI:135676) has functional parent cinnamic acid (CHEBI:27386)
Desmosdumotin C (CHEBI:185120) has functional parent cinnamic acid (CHEBI:27386)
ethyl p-methoxycinnamate (CHEBI:29015) has functional parent cinnamic acid (CHEBI:27386)
feruloylacetic acid (CHEBI:71303) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide A (CHEBI:221683) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide B (CHEBI:221688) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide C (CHEBI:221693) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide E (CHEBI:221702) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide G (CHEBI:221712) has functional parent cinnamic acid (CHEBI:27386)
Hancockiamide I (CHEBI:221721) has functional parent cinnamic acid (CHEBI:27386)
Lahorenoic acid A (CHEBI:200439) has functional parent cinnamic acid (CHEBI:27386)
Lahorenoic acid B (CHEBI:227177) has functional parent cinnamic acid (CHEBI:27386)
Linderone (CHEBI:178327) has functional parent cinnamic acid (CHEBI:27386)
LSM-24504 (CHEBI:113094) has functional parent cinnamic acid (CHEBI:27386)
LSM-31444 (CHEBI:120001) has functional parent cinnamic acid (CHEBI:27386)
LSM-36615 (CHEBI:125150) has functional parent cinnamic acid (CHEBI:27386)
LSM-36617 (CHEBI:125152) has functional parent cinnamic acid (CHEBI:27386)
LSM-36623 (CHEBI:125158) has functional parent cinnamic acid (CHEBI:27386)
LSM-4526 (CHEBI:93945) has functional parent cinnamic acid (CHEBI:27386)
LSM-4818 (CHEBI:94198) has functional parent cinnamic acid (CHEBI:27386)
LSM-4819 (CHEBI:94199) has functional parent cinnamic acid (CHEBI:27386)
LSM-4820 (CHEBI:94200) has functional parent cinnamic acid (CHEBI:27386)
LSM-4821 (CHEBI:94201) has functional parent cinnamic acid (CHEBI:27386)
LSM-4925 (CHEBI:94296) has functional parent cinnamic acid (CHEBI:27386)
LSM-6206 (CHEBI:94982) has functional parent cinnamic acid (CHEBI:27386)
LSM-6645 (CHEBI:95297) has functional parent cinnamic acid (CHEBI:27386)
LSM-6681 (CHEBI:95325) has functional parent cinnamic acid (CHEBI:27386)
Lucidone (CHEBI:183569) has functional parent cinnamic acid (CHEBI:27386)
methyl 4-hydroxy-2-oxo-4-phenyl-3-butenoate (CHEBI:137095) has functional parent cinnamic acid (CHEBI:27386)
N-(1-cinnamoylpyrrolidin-2-yl)cinnamamide (CHEBI:217917) has functional parent cinnamic acid (CHEBI:27386)
N-(2-methoxyethyl)-3-phenyl-N-[5-(3-pyridinyl)-1,3,4-thiadiazol-2-yl]-2-propenamide (CHEBI:115530) has functional parent cinnamic acid (CHEBI:27386)
N-(4,5-dihydrothiazol-2-yl)-3-(2,4-dimethoxyphenyl)-2-propenamide (CHEBI:125330) has functional parent cinnamic acid (CHEBI:27386)
N-(4,5-dihydrothiazol-2-yl)-3-(4-methylphenyl)-2-propenamide (CHEBI:95301) has functional parent cinnamic acid (CHEBI:27386)
N-(4,5-dihydrothiazol-2-yl)-3-(4-propan-2-ylphenyl)-2-propenamide (CHEBI:95278) has functional parent cinnamic acid (CHEBI:27386)
N-[6-acetamido-3-(2-ethoxyethyl)-1,3-benzothiazol-2-ylidene]-3-(2-chlorophenyl)-2-propenamide (CHEBI:114912) has functional parent cinnamic acid (CHEBI:27386)
N-[[(1-oxo-2-thiophen-2-ylethyl)hydrazo]-sulfanylidenemethyl]-3-phenyl-2-propenamide (CHEBI:111379) has functional parent cinnamic acid (CHEBI:27386)
N-[[(4-methyl-2-pyridinyl)amino]-sulfanylidenemethyl]-3-phenyl-2-propenamide (CHEBI:121419) has functional parent cinnamic acid (CHEBI:27386)
N-[[[2-furanyl(oxo)methyl]hydrazo]-sulfanylidenemethyl]-3-(4-methoxyphenyl)-2-propenamide (CHEBI:114312) has functional parent cinnamic acid (CHEBI:27386)
N-cyclohexyl-3-(3,4-dimethoxyphenyl)-N-(2-pyridinyl)-2-propenamide (CHEBI:116516) has functional parent cinnamic acid (CHEBI:27386)
N-cyclohexyl-3-(4-nitrophenyl)-N-(2-pyridinyl)-2-propenamide (CHEBI:107459) has functional parent cinnamic acid (CHEBI:27386)
N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]-2-propenamide (CHEBI:94531) has functional parent cinnamic acid (CHEBI:27386)
N-methyl-3-(2-nitrophenyl)-N-(thiophen-2-ylmethyl)-2-propenamide (CHEBI:120404) has functional parent cinnamic acid (CHEBI:27386)
N-trans-cinnamoyl 2-amino-3a,4,5,6,7,8,9,10,11,12,13,13a-dodecahydrocyclododeca[d]oxazole (CHEBI:197880) has functional parent cinnamic acid (CHEBI:27386)
Swerilactone O (CHEBI:69299) has functional parent cinnamic acid (CHEBI:27386)
Syzygiol (CHEBI:137879) has functional parent cinnamic acid (CHEBI:27386)
Xenocockiamide B (CHEBI:221731) has functional parent cinnamic acid (CHEBI:27386)
Xenocockiamide C (CHEBI:221735) has functional parent cinnamic acid (CHEBI:27386)
Xenocockiamide D (CHEBI:221741) has functional parent cinnamic acid (CHEBI:27386)
cis-cinnamic acid (CHEBI:35699) is a cinnamic acid (CHEBI:27386)
trans-cinnamic acid (CHEBI:35697) is a cinnamic acid (CHEBI:27386)
cinnamate (CHEBI:23248) is conjugate base of cinnamic acid (CHEBI:27386)
IUPAC Name
3-phenylprop-2-enoic acid
Synonyms Sources
3-phenyl-2-propenoic acid NIST Chemistry WebBook
3-phenylacrylic acid NIST Chemistry WebBook
3-phenylpropenoic acid ChEBI
benzenepropenoic acid ChemIDplus
benzylideneacetic acid ChemIDplus
β-phenylacrylic acid NIST Chemistry WebBook
Cinnamic acid KEGG COMPOUND
PhCH=CHCO2H ChEBI
phenylacrylic acid NIST Chemistry WebBook
Zimtsäure ChEBI
Manual Xrefs Databases
C10438 KEGG COMPOUND
Cinnamic_acid Wikipedia
HMDB0000567 HMDB
View more database links
Registry Numbers Types Sources
328659 Gmelin Registry Number Gmelin
507757 Reaxys Registry Number Reaxys
621-82-9 CAS Registry Number KEGG COMPOUND
621-82-9 CAS Registry Number ChemIDplus
621-82-9 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
19238838 PubMed citation Europe PMC
24636064 PubMed citation Europe PMC
24868863 PubMed citation Europe PMC
7628877 PubMed citation Europe PMC
Last Modified
17 November 2016